Preparative-scale synthesis of 3,3,3-trifluoropropene oxide

Ramachandran, P. Veeraraghavan; Padiya, Kamlesh J.

doi:10.1016/j.jfluchem.2007.05.018

Cited by 7 publications

(3 citation statements)

References 23 publications

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“…A drawback of this procedure involves the high cost of the optically pure starting material, and the preparation of racemic 3,3,3-trifluoropropylene oxide elongates this synthetic procedure substantially. 8 In a second approach, 1alkyl-2-(trifluoromethyl)aziridines have been prepared by the reaction of (b-trifluoromethyl)vinyl diphenyl sulfonium triflate with different alkylamines. 6j This (b-trifluoromethyl)vinyl diphenyl sulfonium triflate was synthesized starting from 3,3,3-trifluoro-2bromopropene, which was converted by an addition-elimination reaction with thiophenol into phenyl (b-trifluoromethyl)vinyl sulfide.…”

Section: Introductionmentioning

confidence: 99%

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

et al. 2011

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An efficient and straightforward approach towards the synthesis of 1-alkyl-2-(trifluoromethyl)-aziridines starting from 1,1,1-trifluoroacetone via imination, α-chlorination, hydride reduction and ring closure, was developed. In addition, novel primary β-iodo amines were obtained by regioselective ring opening of these 2-(trifluoromethyl)aziridines using alkyl iodides, and their synthetic potential was demonstrated by converting them into novel α-CF 3 -β-phenylethylamines upon treatment with lithium diphenylcuprate.

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Section: Introductionmentioning

confidence: 99%

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

et al. 2011

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“…β-(Trifluoromethyl)vinyl sulfonium salts 1 and 2 were readily prepared from commercially available 3,3,3-trifluoropropene in five steps, as illustrated in Scheme . Intermediate 3 was readily prepared in two steps in 40 g scale according to the reported literature procedure from 3,3,3-trifluoropropene . Esterification of the resulting alcohol with 1.2 equiv of triflic anhydride and 1.2 equiv of pyridine in CH 2 Cl 2 gave intermediate 4 in quantitative yield.…”

Section: Resultsmentioning

confidence: 99%

β-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds

2011

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Two trifluoromethyl-substituted building blocks β-(trifluoromethyl)vinyl sulfonium salts 1 and 2 were developed. Reactions of β-(trifluoromethyl)vinyl sulfonium salt 1 with active methylene compounds containing electron-withdrawing groups using DBU as the base in DMSO occurred to give trifluoromethyl-substituted cyclopropane derivatives 7 as the major products. In contrast, reactions of β-(trifluoromethyl)vinyl sulfonium salt 2 with active methylene compounds occurred with the migration of one of the electron-withdrawing groups to give the products 8 as the major products when NaH was used as the base in DMSO. Moreover, when NaH was used as base in THF/CH(2)Cl(2) at -78 °C, reaction of β-(trifluoromethyl)vinyl sulfonium salt 1 gave trifluoromethyl-substituted 2,3-dihydrofuran derivatives 9 as the major products. A working mechanism was proposed to explain the different behaviors of the β-(trifluoromethyl)vinyl sulfonium salts 1 or 2 with active methylene compounds under these different conditions.

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“…However, only limited methods for the transformations of TFP have been reported so far. Generally, these methods mainly focus either on the mono-functionalization of TFP, such as hydrofunctionalization 12 – 16 , or on the simple functionalization of TFP that produces limited types of products, such as polymerization 3 , 5 , 17 , 18 and expoxidation 19 , 20 (Fig. 1a ).…”

Section: Introductionmentioning

confidence: 99%

Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene

Wang

Zhang

2022

Commun Chem

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Owing to the versatile synthetic utility of its carbon-carbon double bond, low-cost industrial chemical 3,3,3-trifluoropropene (TFP) represents one of the most straightforward and cost-efficient precursors to prepare trifluoromethylated compounds. However, only limited methods for the efficient transformations of TFP have been reported so far. Here, we report a nickel-catalyzed dicarbofunctionalization of TFP. The reaction uses inexpensive NiCl2·6H2O as the catalyst and 4,4’-biMeO-bpy and PCy2Ph as the ligands, allowing the alkyl-arylation of TFP with a variety of tertiary alkyl iodides and arylzinc reagents in high efficiency. This nickel-catalyzed process overcomes the previous challenges by suppressing β-H and β-F eliminations from TFP, rendering this strategy effective for the transformations of TFP into medicinal interest trifluoromethylated compounds.

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Preparative-scale synthesis of 3,3,3-trifluoropropene oxide

Cited by 7 publications

References 23 publications

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

Straightforward synthesis of 1-alkyl-2-(trifluoromethyl)aziridines starting from 1,1,1-trifluoroacetone

β-(Trifluoromethyl)vinyl Sulfonium Salts: Preparation and Reactions with Active Methylene and Methenyl Compounds

Nickel-catalyzed alkyl-arylation of 3,3,3-trifluoropropene

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